US2013252811A1PendingUtilityA1
Novel herbicide
Est. expiryDec 17, 2029(~3.4 yrs left)· nominal 20-yr term from priority
A01N 47/06A01N 43/16A01N 43/66C07D 309/30A01N 43/653A01N 43/54A01N 43/80
43
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Claims
Abstract
Herbicidal composition comprising a pyrandione herbicide and a co-herbicide The present invention relates to a herbicidal composition comprising as active ingredient a mixture of a) a herbicidally effective amount of a compound of formula (I) wherein: R 1 is methyl, ethyl, n-propyl, halogen, difluoromethoxy, trifluoromethoxy or trifluoromethyl, R 2 is phenyl or phenyl substituted by C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or halogen, R 4 , R 5 , R 6 and R 7 , independently of each other, are hydrogen or C 1 -C 4 alkyl, Y is O, and G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, or ammonium, or G is a latentiating group which is C(O)—R a or C(0)-O—R b ; and b) a co-herbicide selected from the group consisting of fenoxasulfone, ipfencarbazone, propyrisulfuron, and N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide. The herbicidal composition is typically for controlling grasses and weeds in crops of useful plants, especially for controlling Echinochloa and/or Leptochloa weeds in crops of rice.
Claims
exact text as granted — not AI-modified1 . A herbicidal composition comprising as active ingredient a mixture of:
a) a herbicidally effective amount of a compound of formula (I)
wherein:
R 1 is methyl, ethyl, n-propyl, halogen, difluoromethoxy, trifluoromethoxy or trifluoromethyl,
R 2 is phenyl or phenyl substituted by C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or halogen,
R 4 , R 5 , R 6 and R 7 , independently of each other, are hydrogen or C 1 -C 4 alkyl,
Y is O, and
G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, or ammonium, or G is a latentiating group which is C(O)—R a or C(O)—O—R b ;
wherein R a is H, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, C 1 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 1 -C 10 aminoalkyl, C 1 -C 5 alkylaminoC 1 -C 5 alkyl, C 2 -C 8 dialkylaminoC 1 -C 5 alkyl, C 3 -C 7 cycloalkylC 1 -C 5 alkyl, C 1 -C 5 alkoxyC 1 -C 5 alkyl, C 3 -C 5 alkenyloxyC 1 -C 5 alkyl, C 3 -C 5 alkynyloxyC 1 -C 5 alkyl, C 1 -C 5 alkylthioC 1 -C 5 alkyl, C 1 -C 5 alkylsulfinylC 1 -C 5 alkyl, C 1 -C 5 alkylsulfonylC 1 -C 5 alkyl, C 2 -C 8 alkylideneaminoxyC 1 -C 5 alkyl, C 1 -C 5 alkylcarbonylC 1 -C 5 alkyl, C 1 -C 5 alkoxycarbonylC 1 -C 5 alkyl, aminocarbonylC 1 -C 5 alkyl, C 1 -C 5 alkylaminocarbonylC 1 -C 5 alkyl, C 2 -C 8 dialkylaminocarbonylC 1 -C 5 alkyl, C 1 -C 5 alkylcarbonylaminoC 1 -C 5 alkyl, N—C 1 -C 5 alkylcarbonyl-N—C 1 -C 5 alkylaminoC 1 -C 5 alkyl, C 3 -C 6 -trialkylsilylC 1 -C 5 alkyl, phenylC 1 -C 5 alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroarylC 1 -C 5 alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 2 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro; and
R b is C 1 -C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 18 alkynyl, C 2 -C 10 haloalkyl, C 1 -C 10 cyanoalkyl, C 1 -C 10 nitroalkyl, C 2 -C 10 aminoalkyl, C 1 -C 5 alkylaminoC 1 -C 5 alkyl, C 2 -C 8 dialkylaminoC 1 -C 5 alkyl, C 3 -C 7 cycloalkylC 1 -C 5 alkyl, C 1 -C 5 alkoxyC 1 -C 5 alkyl, C 3 -C 5 alkenyloxyC 1 -C 5 alkyl, C 3 -C 5 alkynyloxyC 1 -C 5 alkyl, C 1 -C 5 alkylthioC 1 -C 5 alkyl, C 1 -C 5 alkylsulfinylC 1 -C 5 alkyl, C 1 -C 5 alkylsulfonylC 1 -C 5 alkyl, C 2 -C 8 alkylideneaminoxyC 1 -C 5 alkyl, C 1 -C 5 alkylcarbonylC 1 -C 5 alkyl, C 1 -C 5 alkoxycarbonylC 1 -C 5 alkyl, aminocarbonylC 1 -C 5 alkyl, C 1 -C 5 alkylaminocarbonylC 1 -C 5 alkyl, C 2 -C 8 dialkylaminocarbonylC 1 -C 5 alkyl, C 1 -C 5 alkylcarbonylaminoC 1 -C 5 alkyl, N—C 1 -C 5 alkylcarbonyl-N—C 1 -C 5 alkylaminoC 1 -C 5 alkyl, C 3 -C 6 -trialkylsilylC 1 -C 5 alkyl, phenylC 1 -C 5 alkyl (wherein the phenyl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), heteroarylC 1 -C 5 alkyl (wherein the heteroaryl is optionally substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl, halogen, cyano, or by nitro), C 3 -C 5 haloalkenyl, C 3 -C 8 cycloalkyl, phenyl or phenyl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, halogen, cyano or nitro;
and
b) a co-herbicide selected from the group consisting of fenoxasulfone, ipfencarbazone, propyrisulfuron, and N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide.
2 . A herbicidal composition as claimed in claim 1 , wherein R 1 is ethyl.
3 . A herbicidal composition as claimed in claim 1 , wherein R 2 is phenyl substituted by methyl, methoxy, or halogen.
4 . A herbicidal composition as claimed in claim 3 , wherein R 2 is phenyl substituted by fluorine or chlorine.
5 . A herbicidal composition as claimed in claim 1 , wherein R 4 , R 5 , R 6 and R 7 , independently of each other, are hydrogen or C 1 -C 2 alkyl.
6 . A herbicidal composition as claimed in claim 5 , wherein R 4 , R 5 , R 6 and R 7 are methyl.
7 . A herbicidal composition as claimed in claim 1 , wherein G is hydrogen, C(O)—R a or C(O)—O—R b ; wherein R a and R b are C 1 -C 6 alkyl.
8 . A herbicidal composition as claimed in claim 7 , wherein G is hydrogen, C(O)—R a or C(O)—O—R b ; wherein R a and R b are methyl, ethyl, n-propyl, isopropyl or t-butyl.
9 . A herbicidal composition as claimed in claim 8 , wherein G is hydrogen.
10 . A herbicidal composition as claimed in claim 1 , wherein the compound of formula (I) is:
11 . A herbicidal composition as claimed in claim 10 , wherein the compound of formula (I) is compound A-4, A-7 or A-9.
12 . A herbicidal composition as claimed in claim 1 , wherein the co-herbicide is fenoxasulfone or ipfencarbazone.
13 . A herbicidal composition as claimed in claim 1 , wherein the co-herbicide is fenoxasulfone.
14 . A herbicidal composition as claimed in claim 1 , wherein the co-herbicide is ipfencarbazone.
15 . A herbicidal composition as claimed in claim 1 , wherein the co-herbicide is propyrisulfuron.
16 . A herbicidal composition as claimed in claim 1 , wherein the co-herbicide is N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide.
17 . A herbicidal composition as claimed in claim 11 , wherein the co-herbicide is fenoxasulfone or ipfencarbazone.
18 . A herbicidal composition as claimed in claim 11 , wherein the co-herbicide is fenoxasulfone.
19 . A herbicidal composition as claimed in claim 18 , wherein the compound of formula (I) is compound A-4, and the co-herbicide is fenoxasulfone.
20 . A herbicidal composition as claimed in claim 18 , wherein the compound of formula (I) is compound A-7, and the co-herbicide is fenoxasulfone.
21 . A herbicidal composition as claimed in claim 18 , wherein the compound of formula (I) is compound A-9, and the co-herbicide is fenoxasulfone.
22 . A herbicidal composition as claimed in claim 1 , wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 1:6 to 3:2.
23 . A herbicidal composition as claimed in any claim 22 , wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 1:4 to 4:5.
24 . A herbicidal composition as claimed in claim 23 , wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 3:10 to 7:10.
25 . A herbicidal composition as claimed in claim 24 , wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 2:5 to 7:10.
26 . A herbicidal composition as claimed in claim 25 , wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 1:2 to 7:10.
27 . A herbicidal composition as claimed in claim 11 , wherein the co-herbicide is ipfencarbazone.
28 . A herbicidal composition as claimed in claim 1 , wherein the weight ratio of the compound of formula (I) to the ipfencarbazone is from 1:7 to 1:1.
29 . A herbicidal composition as claimed in claim 28 , wherein the weight ratio of the compound of formula (I) to the ipfencarbazone is from 6:25 to 1:2.
30 . A herbicidal composition as claimed in claim 11 , wherein the co-herbicide is propyrisulfuron.
31 . A herbicidal composition as claimed in claim 1 , wherein the weight ratio of the compound of formula (I) to the propyrisulfuron is from 1:2 to 3:1.
32 . A herbicidal composition as claimed in claim 31 , wherein the weight ratio of the compound of formula (I) to the propyrisulfuron is from 3:4 to 3:2.
33 . A herbicidal composition as claimed in claim 11 , wherein the co-herbicide is N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide.
34 . A herbicidal composition as claimed in claim 1 , wherein the weight ratio of the compound of formula (I) to the N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide is from 1:20 to 20:1.
35 . A herbicidal composition as claimed in claim 1 , which is a formulation comprising a carrier, a solvent and/or a surface-active substance.
36 . A herbicidal composition as claimed in claim 35 , wherein the formulation is in the form of a wettable powder, a water-dispersible granule, an emulsifiable concentrate, a microemulsifiable concentrate, an oil-in-water emulsion, an oil flowable, an aqueous dispersion, an oily dispersion, a soluble liquid, or a water-soluble concentrate wherein the water-soluble concentrate is with water or a water-miscible organic solvent as carrier.
37 . A herbicidal composition as claimed in claim 36 , wherein the formulation is in the form of an emulsifiable concentrate.
38 . A herbicidal composition as claimed in claim 1 , comprising c) a safener and, optionally, d) an oil additive.
39 . A herbicidal composition as claimed in to claim 38 comprising c) a safener selected from cloquintocet-mexyl and mefenpyr-diethyl.
40 . A herbicidal composition as claimed in claim 1 , which is for controlling grasses and weeds in crops of useful plants.
41 . A herbicidal composition as claimed in claim 40 , which is for controlling grasses and weeds in crops of rice.
42 . A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidal composition as defined in claim 1 to the plants or to the locus thereof.
43 . A method as claimed in claim 42 , wherein the crops of useful plants are crops of rice.
44 . A method as claimed in claim 43 , wherein the crops of useful plants are crops of flooded transplanted rice.
45 . A method as claimed in claim 42 , wherein the grasses and weeds controlled comprise Echinochloa and/or Leptochloa.
46 . A method as claimed in claim 42 , wherein the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 30 to 240 g of the compound of formula (I) per hectare, calculated as the weight of the compound of formula (I) excluding the weight of any optional counterions thereof.
47 . A method as claimed in claim 46 , wherein the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 50 to 150 g of the compound of formula (I) per hectare, calculated as the weight of the compound of formula (I) excluding the weight of any optional counterions thereof.
48 . A method as claimed in claim 42 , wherein the co-herbicide is fenoxasulfone, ipfencarbazone, or propyrisulfuron; and
when the co-herbicide is fenoxasulfone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 100 to 400 g of fenoxasulfone per hectare, calculated as the weight of fenoxasulfone excluding the weight of any optional counterions thereof; and when the co-herbicide is ipfencarbazone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 100 to 500 g of ipfencarbazone per hectare, calculated as the weight of ipfencarbazone excluding the weight of any optional counterions thereof; and when the co-herbicide is propyrisulfuron, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 40 to 160 g of propyrisulfuron per hectare, calculated as the weight of propyrisulfuron excluding the weight of any optional counterions thereof.
49 . A method as claimed in claim 48 , wherein the co-herbicide is fenoxasulfone, ipfencarbazone, or propyrisulfuron; and
when the co-herbicide is fenoxasulfone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 200 g of fenoxasulfone per hectare, calculated as the weight of fenoxasulfone excluding the weight of any optional counterions thereof; and when the co-herbicide is ipfencarbazone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 250 g of ipfencarbazone per hectare, calculated as the weight of ipfencarbazone excluding the weight of any optional counterions thereof; and when the co-herbicide is propyrisulfuron, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 80 g of propyrisulfuron per hectare, calculated as the weight of propyrisulfuron excluding the weight of any optional counterions thereof.
50 . A method of controlling Leptochloa weeds in crops of useful plants, which comprises applying compound A-9, whose structure is
to the plants or to the locus thereof.Join the waitlist — get patent alerts
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